Synthesis and evaluation of some new 1,3,4-oxadiazoles bearing thiophene, thiazole, coumarin, pyridine and pyridazine derivatives as antiviral agents.
Identifieur interne : 000C47 ( PubMed/Curation ); précédent : 000C46; suivant : 000C48Synthesis and evaluation of some new 1,3,4-oxadiazoles bearing thiophene, thiazole, coumarin, pyridine and pyridazine derivatives as antiviral agents.
Auteurs : Mohammed Albratty [Arabie saoudite] ; Karam Ahmed El-Sharkawy [Arabie saoudite] ; Hassan Ahmed Alhazmi [Arabie saoudite]Source :
- Acta pharmaceutica (Zagreb, Croatia) [ 1846-9558 ] ; 2019.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Antiviraux, Oxadiazoles.
- synthèse chimique : Antiviraux, Oxadiazoles.
- Antiviraux, Oxadiazoles, Relation structure-activité, Virus.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Oxadiazoles.
- chemical , chemistry : Antiviral Agents, Oxadiazoles.
- chemical , pharmacology : Antiviral Agents, Oxadiazoles.
- drug effects : Viruses.
- Structure-Activity Relationship.
Abstract
In an attempt to produce heterocyclic compounds based on 1,3,4-oxadiazole derivatives with potential antiviral activity, synthesis of compound 1 [2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile] was performed through the reaction of cyanoacetic acid hydrazide with carbon disulfide in alcoholic potassium hydroxide. Compound 1 has an activating methylene group, so it was directed toward some specific reactions. Thus, aryldiazonium chlorides reacted with compound 1 affording hydrazono derivatives 2a-c. Also, aromatic aldehydes reacted with compound 1 to produce compounds 3a,b. Furthermore, cyclic ketones were subjected to the synthesis of fused thiophene derivatives 4a,b via reaction with compound 1 in the presence of elemental sulfur. In addition, 1,3,4-oxadiazole derivative 1, when reacted with isothiocyanates, salicylaldehyde or 1,3-dicarbonyl compounds, formed thiazole derivatives 5a,b, coumarin derivative 6 and alkenyl derivatives 7a,b resp. Compound 7b underwent cyclization to afford pyridine derivative 8. Arylhydrazono derivatives 9a,b were produced through the reaction of compound 7a with aryldiazonium chlorides. Products 9a,b underwent cyclization to produce pyridazine derivatives 10a,b. Finally, 1,3,4-oxadiazole derivative 1 was directed toward reaction with hydrazine derivatives, bromoacetophenone and ethylchloroacetate affording compounds 11a,b, 12 and 13, resp. Fused thiophene derivatives 14a,b were produced via reaction of compounds 4a,b with a mixture of malononitrile and ethylorthoformate. Antiviral activity of the synthesized products showed that 5-(4-amino-3-ethyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione (5a) and 5-(4-amino-3-phenyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione (5b) acted as the most active agents against Feline herpes virus, Feline corona virus, Herpes simplex virus-1 and Herpes simplex virus-2, whereas compound 2-(5-(2-phenylhydrazono)-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile (11b) was the most effective against Vaccinia virus, Herpes simplex virus (TK-KOS-ACVr), Coxsackie virus B4 and Vesicular stomatitis virus.
DOI: 10.2478/acph-2019-0015
PubMed: 31259726
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Box 114 Jazan45142</wicri:regionArea></affiliation></author><author><name sortKey="El Sharkawy, Karam Ahmed" sort="El Sharkawy, Karam Ahmed" uniqKey="El Sharkawy K" first="Karam Ahmed" last="El-Sharkawy">Karam Ahmed El-Sharkawy</name><affiliation wicri:level="1"><nlm:affiliation>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142, Saudi Arabia.</nlm:affiliation><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142</wicri:regionArea></affiliation></author><author><name sortKey="Alhazmi, Hassan Ahmed" sort="Alhazmi, Hassan Ahmed" uniqKey="Alhazmi H" first="Hassan Ahmed" last="Alhazmi">Hassan Ahmed Alhazmi</name><affiliation wicri:level="1"><nlm:affiliation>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142, Saudi Arabia.</nlm:affiliation><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. 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Box 114 Jazan45142, Saudi Arabia.</nlm:affiliation><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142</wicri:regionArea></affiliation></author><author><name sortKey="El Sharkawy, Karam Ahmed" sort="El Sharkawy, Karam Ahmed" uniqKey="El Sharkawy K" first="Karam Ahmed" last="El-Sharkawy">Karam Ahmed El-Sharkawy</name><affiliation wicri:level="1"><nlm:affiliation>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142, Saudi Arabia.</nlm:affiliation><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142</wicri:regionArea></affiliation></author><author><name sortKey="Alhazmi, Hassan Ahmed" sort="Alhazmi, Hassan Ahmed" uniqKey="Alhazmi H" first="Hassan Ahmed" last="Alhazmi">Hassan Ahmed Alhazmi</name><affiliation wicri:level="1"><nlm:affiliation>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142, Saudi Arabia.</nlm:affiliation><country xml:lang="fr">Arabie saoudite</country><wicri:regionArea>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142</wicri:regionArea></affiliation></author></analytic><series><title level="j">Acta pharmaceutica (Zagreb, Croatia)</title><idno type="eISSN">1846-9558</idno><imprint><date when="2019" type="published">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Oxadiazoles (chemical synthesis)</term><term>Oxadiazoles (chemistry)</term><term>Oxadiazoles (pharmacology)</term><term>Structure-Activity Relationship</term><term>Viruses (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Oxadiazoles ()</term><term>Oxadiazoles (pharmacologie)</term><term>Oxadiazoles (synthèse chimique)</term><term>Relation structure-activité</term><term>Virus ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Oxadiazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Oxadiazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Oxadiazoles</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Viruses</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Oxadiazoles</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Oxadiazoles</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><term>Oxadiazoles</term><term>Relation structure-activité</term><term>Virus</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In an attempt to produce heterocyclic compounds based on 1,3,4-oxadiazole derivatives with potential antiviral activity, synthesis of compound 1 [2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile] was performed through the reaction of cyanoacetic acid hydrazide with carbon disulfide in alcoholic potassium hydroxide. Compound 1 has an activating methylene group, so it was directed toward some specific reactions. Thus, aryldiazonium chlorides reacted with compound 1 affording hydrazono derivatives 2a-c. Also, aromatic aldehydes reacted with compound 1 to produce compounds 3a,b. Furthermore, cyclic ketones were subjected to the synthesis of fused thiophene derivatives 4a,b via reaction with compound 1 in the presence of elemental sulfur. In addition, 1,3,4-oxadiazole derivative 1, when reacted with isothiocyanates, salicylaldehyde or 1,3-dicarbonyl compounds, formed thiazole derivatives 5a,b, coumarin derivative 6 and alkenyl derivatives 7a,b resp. Compound 7b underwent cyclization to afford pyridine derivative 8. Arylhydrazono derivatives 9a,b were produced through the reaction of compound 7a with aryldiazonium chlorides. Products 9a,b underwent cyclization to produce pyridazine derivatives 10a,b. Finally, 1,3,4-oxadiazole derivative 1 was directed toward reaction with hydrazine derivatives, bromoacetophenone and ethylchloroacetate affording compounds 11a,b, 12 and 13, resp. Fused thiophene derivatives 14a,b were produced via reaction of compounds 4a,b with a mixture of malononitrile and ethylorthoformate. Antiviral activity of the synthesized products showed that 5-(4-amino-3-ethyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione (5a) and 5-(4-amino-3-phenyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione (5b) acted as the most active agents against Feline herpes virus, Feline corona virus, Herpes simplex virus-1 and Herpes simplex virus-2, whereas compound 2-(5-(2-phenylhydrazono)-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile (11b) was the most effective against Vaccinia virus, Herpes simplex virus (TK-KOS-ACVr), Coxsackie virus B4 and Vesicular stomatitis virus.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31259726</PMID><DateCompleted><Year>2019</Year><Month>11</Month><Day>27</Day></DateCompleted><DateRevised><Year>2019</Year><Month>11</Month><Day>27</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1846-9558</ISSN><JournalIssue CitedMedium="Internet"><Volume>69</Volume><Issue>2</Issue><PubDate><Year>2019</Year><Month>Jun</Month><Day>01</Day></PubDate></JournalIssue><Title>Acta pharmaceutica (Zagreb, Croatia)</Title><ISOAbbreviation>Acta Pharm</ISOAbbreviation></Journal><ArticleTitle>Synthesis and evaluation of some new 1,3,4-oxadiazoles bearing thiophene, thiazole, coumarin, pyridine and pyridazine derivatives as antiviral agents.</ArticleTitle><Pagination><MedlinePgn>261-276</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.2478/acph-2019-0015</ELocationID><ELocationID EIdType="pii" ValidYN="Y">/j/acph.2019.69.issue-2/acph-2019-0015/acph-2019-0015.xml</ELocationID><Abstract><AbstractText>In an attempt to produce heterocyclic compounds based on 1,3,4-oxadiazole derivatives with potential antiviral activity, synthesis of compound 1 [2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile] was performed through the reaction of cyanoacetic acid hydrazide with carbon disulfide in alcoholic potassium hydroxide. Compound 1 has an activating methylene group, so it was directed toward some specific reactions. Thus, aryldiazonium chlorides reacted with compound 1 affording hydrazono derivatives 2a-c. Also, aromatic aldehydes reacted with compound 1 to produce compounds 3a,b. Furthermore, cyclic ketones were subjected to the synthesis of fused thiophene derivatives 4a,b via reaction with compound 1 in the presence of elemental sulfur. In addition, 1,3,4-oxadiazole derivative 1, when reacted with isothiocyanates, salicylaldehyde or 1,3-dicarbonyl compounds, formed thiazole derivatives 5a,b, coumarin derivative 6 and alkenyl derivatives 7a,b resp. Compound 7b underwent cyclization to afford pyridine derivative 8. Arylhydrazono derivatives 9a,b were produced through the reaction of compound 7a with aryldiazonium chlorides. Products 9a,b underwent cyclization to produce pyridazine derivatives 10a,b. Finally, 1,3,4-oxadiazole derivative 1 was directed toward reaction with hydrazine derivatives, bromoacetophenone and ethylchloroacetate affording compounds 11a,b, 12 and 13, resp. Fused thiophene derivatives 14a,b were produced via reaction of compounds 4a,b with a mixture of malononitrile and ethylorthoformate. Antiviral activity of the synthesized products showed that 5-(4-amino-3-ethyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione (5a) and 5-(4-amino-3-phenyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3H)-thione (5b) acted as the most active agents against Feline herpes virus, Feline corona virus, Herpes simplex virus-1 and Herpes simplex virus-2, whereas compound 2-(5-(2-phenylhydrazono)-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile (11b) was the most effective against Vaccinia virus, Herpes simplex virus (TK-KOS-ACVr), Coxsackie virus B4 and Vesicular stomatitis virus.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Albratty</LastName><ForeName>Mohammed</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142, Saudi Arabia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>El-Sharkawy</LastName><ForeName>Karam Ahmed</ForeName><Initials>KA</Initials><AffiliationInfo><Affiliation>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142, Saudi Arabia.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Department of Organic Chemistry Faculty of Biotechnology October University for Modern Sciences and Arts (MSA)El-Wahat Road, 6 October CityEgypt.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Alhazmi</LastName><ForeName>Hassan Ahmed</ForeName><Initials>HA</Initials><AffiliationInfo><Affiliation>Department of Pharmaceutical Chemistry, College of Pharmacy Jazan University, P.O. Box 114 Jazan45142, Saudi Arabia.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>Croatia</Country><MedlineTA>Acta Pharm</MedlineTA><NlmUniqueID>9303678</NlmUniqueID><ISSNLinking>1330-0075</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010069">Oxadiazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>20O2F20OUR</RegistryNumber><NameOfSubstance UI="C583463">1,3,4-oxadiazole</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010069" MajorTopicYN="N">Oxadiazoles</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D014780" MajorTopicYN="N">Viruses</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">1,3,4-oxadiazole derivatives</Keyword><Keyword MajorTopicYN="N">antiviral activity</Keyword><Keyword MajorTopicYN="N">coumarin</Keyword><Keyword MajorTopicYN="N">pyridazine</Keyword><Keyword MajorTopicYN="N">pyridine</Keyword><Keyword MajorTopicYN="N">thiazole</Keyword><Keyword MajorTopicYN="N">thiophene</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="accepted"><Year>2018</Year><Month>11</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2019</Year><Month>7</Month><Day>2</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2019</Year><Month>7</Month><Day>2</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2019</Year><Month>11</Month><Day>28</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">31259726</ArticleId><ArticleId IdType="doi">10.2478/acph-2019-0015</ArticleId><ArticleId IdType="pii">/j/acph.2019.69.issue-2/acph-2019-0015/acph-2019-0015.xml</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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